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WO1996032374A1 - Derives d'acrylonitrile, composition de cristaux liquides et afficheur a cristaux liquides - Google Patents

Derives d'acrylonitrile, composition de cristaux liquides et afficheur a cristaux liquides Download PDF

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Publication number
WO1996032374A1
WO1996032374A1 PCT/JP1996/001012 JP9601012W WO9632374A1 WO 1996032374 A1 WO1996032374 A1 WO 1996032374A1 JP 9601012 W JP9601012 W JP 9601012W WO 9632374 A1 WO9632374 A1 WO 9632374A1
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Prior art keywords
trans
cyclohexyl
fluoro
cyano
group
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PCT/JP1996/001012
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English (en)
Japanese (ja)
Inventor
Atsuko Fujita
Shuichi Matsui
Koichi Shibata
Kazutoshi Miyazawa
Yasuko Sekiguchi
Etsuo Nakagawa
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Chisso Corporation
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Priority to JP53088896A priority Critical patent/JP3498965B2/ja
Priority to US08/930,986 priority patent/US5976408A/en
Priority to EP96909356A priority patent/EP0820983A4/fr
Publication of WO1996032374A1 publication Critical patent/WO1996032374A1/fr

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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
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    • C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
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Definitions

  • the present invention relates to a novel liquid crystal compound, a liquid crystal composition containing the same, and a liquid crystal display device using the composition.
  • the liquid crystal phase includes a nematic liquid crystal phase, a smectic liquid crystal phase, and a cholesteric liquid crystal phase, but the nematic phase is the most common in practical use.
  • the display method in this case includes TN (twisted nematic) type, DS (dynamic scattering) type, guest host type, DAP (alignment phase deformation) type, etc.
  • the liquid crystal compounds used for these have been used up to now.
  • Optical anisotropy and dielectric anisotropy required for Physical properties such as anisotropy and electrical conductivity depend on the display method and the shape of the element, especially in the STN method used in high-quality liquid crystal displays in recent years.
  • the ⁇ of the elastic constant ratio (k33k11) of the liquid crystal composition must be set to a large value, so that it has a large elastic constant, has a wide liquid crystal temperature range, and has a large liquid crystal temperature range.
  • Compounds that have high compatibility, are stable, and have low viscosity so as not to impair the response speed have become important keys.
  • an alkenyl compound represented by the following formula (1) (JP-A-59-176221) is generally known. Since the temperature 15 is narrow, when mixing this in a liquid crystal composition, a compound having a high clearing point must be separately added to compensate for this. However, in general, a compound having a clear point shows a viscosity, so that the above addition results in The viscosity of the entire composition is increased.
  • a cinnamnitrile derivative represented by the formula (2) Japanese Patent Application Laid-Open No. 55-91012
  • Japanese Patent Application Laid-Open No. 55-91012 Japanese Patent Application Laid-Open No. 55-91012
  • a cyanocyclohexane derivative represented by the formula (3) in which a cyano group is directly bonded to a cyclohexane example (Molecular Crystal Liquid Crystal, 111, p. 329, 198, 84) is also known.
  • This compound has high viscosity and a narrow liquid crystal temperature range.
  • new compounds such as difluorovinyl derivative (4) (Japanese Patent Application Laid-Open No. 11-17547) or halogenated vinyl derivative (5) (W093 / 072334) have been developed.
  • the former has low viscosity but low reliability, and has only a narrow liquid crystal range, and the latter has a medium liquid crystal temperature range, but still has low reliability and is not practical. Therefore, the development of a new low-viscosity, high-reliability material having a large elastic constant value and a high clearing point has been awaited.
  • An object of the present invention is to solve the above-mentioned drawbacks of the prior art and to maintain excellent properties as a liquid crystal component, namely, a wide liquid crystal temperature range, good compatibility with other liquid crystals, and low viscosity.
  • An object of the present invention is to provide a novel liquid crystalline compound capable of giving a large elastic constant furnace, a liquid crystal composition containing the same, and a liquid crystal display device comprising the composition.
  • the present invention has the following features.
  • ISA ', ⁇ A 2 and YA 3 may be ⁇ by one or two fluorine atoms each independently 1, 4 one-phenylene, 1, 4-xylene to Shikuro,
  • R ′ is a cyano group, a halogen atom, or an alkyl when iSA 1 is 1,4-phenylene; Groups, alkoxy groups, alkyl groups with one or more fluorine atoms,
  • 3 ⁇ 4 ⁇ represents 1,4-cyclohexylene. However, two or more heterozygotes are not included in the molecule at the same time.
  • R ′ is an alkyl group, an alkoxy group or an alkoxyalkyl group
  • a ′, SA 2 and 3ESA 3 are 1,4-phenylene or 1,4-cyclohexylene, which may be S ⁇ with one or two fluorine atoms. Lilonitryl derivatives.
  • Either ⁇ 1 or ⁇ 2 is 0, ⁇ 2 and ⁇ 3 are each independently a covalent bond or 1.2-ethylene, and R 2 is a group represented by formula II The acrylonitrile derivative according to (5).
  • ⁇ 1 and Ti 2 is 0, ⁇ 2 and ⁇ 3 are each independently a covalent bond or 1,2-ethylene, and R 2 is a group represented by the formula [ ⁇ ] An acrylonitrile derivative according to (5).
  • (1 0) ⁇ ' may be substituted by 1 or 2 fluorine atoms.1-Phenylene.R' is substituted by a thiono group, a halogen atom or one or more fluorine atoms. Or a substituted alkoxy group substituted with one or more fluorine atoms.
  • JSA 1 may be replaced by one or two fluorine atoms.
  • SA 1 is 1,4-phenylene which may be substituted with one or two fluorine atoms.
  • R 1 is substituted with a silane group, a halogen atom, and one or more fluorine atoms Alkyl group or alkoxy group substituted with one or more fluorine atoms
  • accession Rironito according to R 2 is a group represented by the formula III (1 3) Lil derivative.
  • a liquid crystal composition comprising at least two components, comprising at least one liquid crystal compound represented by the general formula I.
  • the first component has at least one acrylonitrile derivative according to any one of (1) to (16), and the second component has the general formula IV, V and VI
  • R 3 represents an alkyl group having 1 to 10 carbon atoms
  • Y represents a fluorine or chlorine atom
  • Q ′ and Q 2 each independently represent a hydrogen or a fluorine atom
  • m represents 1 or
  • Z 1 and Z 2 each independently represent one CH 2 CH 2 one or a covalent bond.
  • any methylene group (one CH 2 —) is an oxygen atom (one ), but no two or more methylene groups are consecutively linked to an oxygen atom
  • Z 3 represents one CH 2 CH 2 , one COO— or a covalent bond
  • Q 3 represents a hydrogen or fluorine atom
  • ⁇ C represents 1,4-cyclohexylene, 1,4-phenylene or 1.3-dioxane-1-2.5-diyl
  • 1 represents 0 or 1.
  • Rs represents an alkyl group having 1 to 10 carbon atoms
  • 0 represents 0 or 1.
  • R 6 represents a alkyl group having a prime number of 1 to 10, represents 1,4-cyclohexylene or 1,4-phenylene, and Q 5 and Q 6 represent a hydrogen atom or a fluorine atom, respectively. shows, Zeta 4 shows an C_rei_0- or a covalent bond, p is 0 or 1.
  • R 7 and R e each independently represent an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms.
  • any methylene group (one CH 2 — ) May be g-substituted by an oxygen atom, but two or more methylene groups are not consecutively substituted by an oxygen atom ⁇ E is 1,4-cyclohexylene, 1.3— Birimidine mono 2,5-diyl or 1.4-phenylene, SF represents 1,4-cyclohexylene or 1,4-phenylene, Z 5 represents one C ⁇ C one, one COO—, -CH a CH 2 — or indicates a covalent bond.)
  • R 3 represents an alkyl group having 1 to 10 carbon atoms or a alkoxy group
  • R 1 represents Represents an alkyl group, an alkoxy group or an alkoxymethyl group having 1 to 10 carbon atoms
  • 3 ⁇ 41 and SJ are each independently Represents 1.4-cyclohexylene or 1.4-phenylene
  • Z 6 represents one C ⁇ , -CH 2 CH 2 or a covalent bond
  • Z 7 represents one C ⁇ C one, one It represents CO ⁇ — or a covalent bond
  • Q 7 represents a hydrogen or fluorine atom.
  • a liquid crystal composition comprising one or more compounds selected from the group consisting of:
  • liquid crystal compound according to any one of (1) to (16) is contained, and as a part of the second component, it is composed of general formulas IV, V and VI Contain at least one compound selected from the group and at least one compound selected from the group consisting of the general formulas VII, VIII, IX, X and XI as the other part of the second component
  • a liquid crystal composition characterized by the following.
  • a liquid crystal display device comprising the liquid crystal composition according to any one of (17) to (20).
  • the acritic nitrile derivative of the present invention represented by the general formula I can be represented by a compound of the formula ⁇ from the following formula XVI I when attention is paid to the molecular terminal.
  • the compounds of formulas XVI I and XIX having a cyanoethylene group at the molecular end are stable to heat and ultraviolet light, and do not deteriorate under the normal use conditions even when sealed in a liquid crystal panel.
  • Compounds having a conjugated gen chain at the molecular terminal represented by the formulas XXI, XXI XXIII and ⁇ have a large elastic constant ratio and are useful.
  • the fluorine-containing compounds represented by the formulas (VIII, XX, ⁇ , and ⁇ ) have a wide liquid crystal temperature range and a particularly low viscosity, and are useful compounds.
  • the so-called 2S compound represented by the formula XXV can set its liquid crystal range around room temperature among the compounds of the present invention, and hardly precipitates crystals when used as a component of the liquid crystal composition.
  • the two compounds have a lower viscosity compared to other 3S or 4S structures, so that when they are enclosed in a liquid crystal panel, a fast response speed can be obtained.
  • the so-called 3-compound represented by the formula XXVI has a clear point, shows good compatibility, and has a large elastic constant ratio necessary for obtaining good steepness.
  • All compounds of the formula XXVI I having a 4 ⁇ structure are non- To have ⁇ I clearing point, have a large elastic constant ratio is important as a constituent of the composition exhibits a ⁇ relatively large optical anisotropy.
  • XXV—1 to XXV—4 represent combinations of S structures exhibiting more preferable characteristics among the 2S compounds represented by Formula XXV
  • VI— represent combinations of structures exhibiting more desirable characteristics among the trifunctional compounds represented by Formula XXVI. 1 to XXVI-12, and further, among the tetrafunctional compounds represented by the formula XXVI I, combinations of 3 ⁇ 4 structures showing more preferable properties are shown in XXVI I-1 to XXVI I-24.
  • V — 1, XVI-5, 6, 7, 8, 9, 10 and VII-11, 5, 6, 7, 8, 9, 10, 13 to 24, to cyclo Compounds having two or more siloxanes S in the molecule are useful because they have a wide liquid crystal temperature range, low viscosity, and low viscosity.
  • Compounds having a hetero S represented by 12, 14, 16, 16, 18, 20, 21, 22, 23, and 24 all show large dielectric anisotropy values and are constituents of liquid crystal compositions. As important.
  • the compounds represented by XXV-3, XXVI-2, 3, 4 and 11-1, 2, 3, 4, 13, 14, 14, 15 and 16 have a substituent on the phenyl group.
  • a compound suitable for the purpose can be provided.
  • Preferred examples of the fuunyl group into which the g ⁇ group has been introduced are shown in formulas i to xxvii. "
  • All of the compounds of the present invention having a terminal at the terminal have a large dielectric anisotropy value, a low viscosity and a wide liquid crystal range, and are particularly important compounds for giving a liquid crystal composition dielectric properties. It is.
  • the compound of the present invention having a phenyl S represented by the formula xxii to xjcvii having an electron-withdrawing substituent as described above on the phenyl and one or two fluorine atoms further has a larger dielectric constant. It has anisotropy and is an indispensable material for low-voltage driving of liquid crystal display devices.
  • the compounds of the present invention having a phenyl group (i to iii) into which a weakly electron-donating group such as an alkyl group, an alkoxy group or an alkoxyalkyl group are introduced are compounds having no large dipole moment. These compounds are characterized by low viscosity and good compatibility, and are useful in that they can be used for adjusting the physical properties of the entire liquid crystal composition to required values.
  • the compounds represented by XXV — a, XXVI — ah, XXVI — 0, p and XXVI I — as have at least one covalent bond as an intermediate group. They exhibit low viscosity and good compatibility.
  • Compounds of the formulas V — b, XXVI — b, hm and XXVI I — b, h, n with ethylene chains or other bonds together as intermediate groups show good liquid crystallinity and low viscosity, Good compatibility.
  • ethenylene derivatives such as those represented by the formulas XXV — g, XXV I-f.m and ⁇ -1 f, 1 have a particularly wide liquid crystal temperature range and low viscosity.
  • this when this is used as a component of the liquid crystal composition, it has an advantage that it does not easily exhibit a smectic phase.
  • butenyl derivatives represented by the formulas XXV—h, ⁇ —g, ⁇ and XXVI I g, m, s are preferred compounds exhibiting good compatibility and low viscosity.
  • the compound of the present invention represented by the formula I can be synthesized, for example, by a method shown below.
  • a good yield can be obtained by reacting at low temperature in a polar polar solvent.
  • the product in this reaction may be obtained as a mixture of two isomers derived from the double bond, i.e., ⁇ -isomer and ⁇ -isomer. If necessary, this is purified by recrystallization, distillation, etc. By applying the separation simulation, it is possible to singly dispose only the liquid crystal material having better characteristics.
  • R ′, A ′, B ′, A 3 , n KB 2 , A 3 , n 2, B 3 and n 3 all have the same meaning as described above, and Y represents iodine or bromine.
  • a metal cyanide in a non-protonic polar solvent.
  • examples of the metal cyanide include cyanide copper and sodium cyanide.
  • this reaction is preferably carried out under the reflux condition of a solvent used in particular. Suitable solvents are cetone, dioxane, dimethylformamide, N-methylbividone, Lysine, tetrahydrofuran and the like can be mentioned.
  • a good yield can be obtained by reacting a monounsaturated aldehyde with a reactant prepared from dimethyl cyanomethylphosphonate and a base in an aprotic polar solvent at a low temperature. Since this reaction proceeds while maintaining the stereo, the starting material, the monounsaturated aldehyde, must be a mixture of stereo isomers or a ⁇ isomer.
  • the product of this reaction may be a mixture of two isomers derived from the newly formed double bond, ie, a ⁇ -isomer and a ⁇ -isomer. It is also possible to apply only a substance having better characteristics as a liquid crystal material to a purification separation simulation such as distillation.
  • R 3 is a group represented by the formula II, and X is a fluorine atom.
  • R ′, ⁇ ′, ⁇ ′, ⁇ 2 ⁇ 1, ⁇ 2 , ⁇ 3 , ⁇ 2, ⁇ 3 and ⁇ 3 each have the same meaning as described above, and ⁇ represents iodine or bromine.
  • the dihalide represented by is cinnaminated in an aprotic solvent such as ⁇ -methylbilidone using a metal sulfide. Since this reaction proceeds while maintaining the steric form, the starting material dihau- gide must be a mixture of isomers or only an isomer.
  • the metal cyanide used in the cyanation reaction sodium cyanide / sodium cyanide is preferable.
  • the reaction is preferably carried out under the reflux condition of the solvent used.
  • R 2 is a group represented by the formula III and X is a fluorine atom: a compound represented by the formula ⁇ —-XXXI,
  • the diha- ⁇ -genated compound represented by is cyanated with a gold-containing compound in an aprotic solvent such as N-methylbilidone. Since this reaction proceeds while maintaining the stereochemistry, the starting material dihalogenated compound must be a mixture containing the ⁇ -isomer or only the ⁇ -isomer.
  • the metal silicide used in the cyanation reaction copper cyanide, sodium cyanide and the like are preferable. This reaction is preferably performed under the reflux conditions of the solvent used, from the viewpoint of good yield.
  • the compound represented by the formula ⁇ among the raw materials used in each of the above-mentioned reactions may be obtained by oxidizing the corresponding alcohol derivative using a suitable oxidizing agent such as PCC, or disclosed in JP-A-1-175947 or It can be produced by a synthetic route as described in W093 / 07234. Further, the halogenated vinyl derivative represented by the formula (1) can be produced by the method described in W093 ⁇ 07234.
  • the ⁇ ,) 9-unsaturated aldehyde represented by the formula ⁇ has the formula XXXIII XXI »when ⁇ 3 is 0.
  • R ', eight', ⁇ 1, A 2, ⁇ 1, ⁇ 2, A 3, are both eta 2 and beta 3 represents. As defined above) after conversion into, and treated with an acid And combine them.
  • the dihalide represented by the formula XXXI can be obtained by treating an aldehyde derivative represented by the formula XXVIII with a reactant prepared from tribromofluoromethane and triphenylphosphine in a suitable solvent such as ethylene glycol dimethyl ether. Obtained.
  • the product in this case is a mixture of ⁇ and ⁇ isomers derived from the stereochemistry of olefin. This product can be used as it is in the next reaction, but if necessary, it can be used for the next reaction after purification by column chromatography or the like to obtain only the antibody.
  • the dihalide represented by ⁇ is obtained by converting ⁇ .9-unsaturated aldehyde represented by formula ⁇ X into tribromofluoromethane and triphenylphosphine in a suitable solvent such as ethylene glycol dimethyl ether. It is obtained by treating with the reactant to be prepared.
  • the product in this case is a mixture of ⁇ and ⁇ isomers derived from the stereochemistry of olefin. This product can be used as it is in the next reaction as it is, but if necessary, it can be used for the next reaction by purifying only the column by performing purification such as column chromatography and ⁇ -matography.
  • liquid crystalline compound I of the present invention has a high clearing point and a large elastic constant ratio (k33 / k11), and is a nematic compound including a TFT method.
  • k33 / k11 a nematic compound including a TFT method.
  • the liquid crystal composition provided by the present invention may be a first component containing at least one kind of the liquid crystal compound represented by the general formula I, but in addition to this, as a second component, the general formula IV described above. , V and VI, and at least one compound selected from the group consisting of Z or general formulas VI I, VI II, IX, X and XI. Compounds (hereinafter, referred to as the second component B) are preferable.
  • threshold pressure, liquid crystal temperature range, optical anisotropy ( ⁇ ), dielectric anisotropy ( ⁇ ) and viscosity For the purpose of adjusting the properties and the like, a known compound can be mixed as the third component.
  • IV-1 to IV-12 as preferred examples of the compound contained in the general formula IV
  • V-1 to V_l8 as the preferred examples of the compound contained in the general formula V
  • Preferable examples of the compound included in the formula VI include VI-1 to VI-18.
  • the compounds represented by these general formulas IV to VI have a positive dielectric anisotropy, have excellent thermal stability and chemical stability, and particularly have a low voltage holding ratio or a specific resistance value. This compound is useful when preparing a liquid crystal composition for TFT (AM-LCD), which requires high reliability, such as large liquid crystal.
  • the compound can be used in an arbitrary range with respect to the total weight of the liquid crystal composition, but is preferably 10 to 97% by weight, more preferably 40 to 97% by weight. 95% by weight.
  • R, R s, R 6 is an alkyl or alkenyl group, R 'represents an alkylene completion.
  • These compounds represented by the general formulas VI1 to IX have a positive dielectric anisotropy and a large value, and are used as a component of the composition, particularly for the purpose of reducing the threshold voltage. It is also used for the purpose of adjusting the viscosity and mass, for widening the nematic temperature eyelashes such as increasing the clearing point, and for further improving the steepness.
  • preferred examples of the compounds contained in the general formulas X and XI include X-1 to X-15 and XI-1 to X13, respectively.
  • R 7 , R e , R 3 and R ′ represent an alkyl group.
  • the compounds represented by the general formulas X and XI are positive compounds having a negative or small dielectric anisotropy.
  • the compound represented by the general formula X is used mainly for adjusting the viscosity reduction of the composition. used.
  • the compound of the general formula XI is used for the purpose of extending the nematic temperature range such as increasing the clearing point of the composition, and / or for the purpose of adjusting ⁇ . Therefore, the compounds of the general formulas VII to XI are particularly useful when preparing a liquid crystal composition for STN display mode or TN display mode.
  • the compound When preparing a liquid crystal composition for a TN display mode or an STN display mode, the compound can be used in an arbitrary amount of 15 depending on the purpose, but is preferably 10 to 97% by weight. Preferably it is 40 to 95% by weight.
  • the preparation of the liquid crystal composition for TFT may be composed of the first component and the second A component, and may partially include the second B component.
  • the liquid crystal composition for STN or TN may be prepared from the first component and the second B component, and may further contain one part of the second A component.
  • the above-mentioned third component may be further added to these liquid crystal compositions according to the purpose.
  • Preferred examples thereof include the following ⁇ -1 to ⁇ -35.
  • the liquid crystal composition provided by the present invention exhibits excellent characteristics when at least one of the liquid crystal compounds represented by the general formula I is contained in a ratio of 0.1 to 99% by weight. Preferred for.
  • the liquid crystal composition of the present invention can be further optimized by adding an appropriate additive depending on the intended use.
  • additives include those described in detail in literatures as chiral additives. This is added to induce the helical structure of the liquid crystal, adjust the required twist angle, and prevent reverse twist.
  • the liquid crystal composition of the present invention optimized in this manner can be prepared by a method known per se, for example, a method in which various liquid crystal compounds contained are dissolved at a temperature higher than room temperature. By injecting the thus-prepared composition into a liquid crystal cell, a liquid crystal display device having a wide operating temperature range, high speed, and responsiveness can be obtained.
  • liquid crystal composition containing the compound of the present invention is exemplified below.
  • Compound No. is the same as that shown in Examples described later.
  • % indicating the content of each compound means wt%.
  • C, N, S A , S D , SE and I represent a crystal phase, a nematic phase, a smectic A phase, a smectic B phase, a smectic E phase and an isotropic liquid phase, respectively.
  • What is indicated by the combination of phases means the transition temperature between the combined phases.
  • CC ' indicates that the transition occurs at the crystal-crystal transition point.
  • Trans-41 (trans-1-ethylcyclohexyl)
  • the title compound was synthesized in the same manner as in Example 1 except that trans-4-formylcyclyl hexyl trans-4-butyl bicyclohexane carboxylate was used as a raw material instead of cyclohexanecarboyl aldehyde.
  • Trans-4-1 (trans-1-ethylcyclohexyl) Example except that trans-1- (4- (4-but-a-biphenyl) butyl) cyclohexanecarbaldehyde is used as a raw material instead of cyclohexanecarbaldehyde
  • the title compound was synthesized in the same manner as in 1.
  • Example 1 except that trans-1- (trans-1-ethylcyclohexyl) cyclohexanecarbaldehyde was replaced by 3- (trans-1- (trans-1-ethylcyclohexyl) cyclohexyl) propanal The title compound was obtained in the same manner.
  • Trans-4-1 (trans-4-ethylcyclohexyl) Same as in Example 1 except that 3- (trans-4- (4-propirphenyl) cyclohexyl) propanal is used as a raw material instead of cyclohexanecarbaldehyde To give the title compound.
  • Trans-1-41 (Trans-1-ethyl J-cyclohexylyl) Substitute for hexadecyl hexaldehyde 3- (Trans-1-41 (2 E- (trans-14-ethylcyclohexyl) ethenyl) Cyclohexyl) Pro
  • the title compound was synthesized in the same manner as in Example 1 except that panal was used as a raw material.
  • Example 1 except that trans-14- (2-formylethyl) cyclohexyl trans-14-ethylcyclohexanecarboxylate was used as a raw material instead of trans-4- (trans-1-ethylcyclohexyl) cyclohexanecarborealdehyde
  • the title compound was synthesized in the same manner as in 1.
  • Example 1 except that trans-1- (trans-1-ethylcyclohexyl) cyclohexanecarboylaldehyde was replaced with 3- (trans-1- (4-ethylphenyl) methoxycyclohexyl) propanal as a raw material
  • the title compound was synthesized in the same manner.
  • Example 1 except that trans-1- (trans-4-ethylcyclohexyl) cyclohexancarbaldehyde is replaced by 3- (trans-1- (4- (4-ethylphenyl) butyl) cyclohexyl) propanal as a raw material
  • the title compound was synthesized in the same manner as in 1.
  • R 1 is an ethyl group, igA 1 is 1.4-cyclo Hexylene, B 1 is a covalent bond, ⁇ 1 is 0, ⁇ 2 is 0, n 3 is 0, R 2 is a compound of the formula III and X is a hydrogen atom (No. 201)].
  • Example 1 (trans-14-ethylhexyl hexyl) Example 1 except that cyclohexanecarbaldehyde was replaced with 3- (trans-14- (trans-4-ethylcyclohexyl) cyclohexyl) 1-2-propenal as a raw material The title compound was obtained in the same manner as in.
  • the starting compound was obtained as follows.
  • the obtained yellow oil was purified using silica gel column chromatography to obtain 1.3 g of colorless crystals. As a result of various analyses, it was confirmed that the product was 1.3-dioxan-2-ylethylidene-trans-141 (trans-14-ethylsilk) cyclohexane.
  • Example 2 1 1-cyano 6— (trans-4-1 (2- (trans-1-ethylcyclohexyl) ethenyl) cyclohexyl) 1-1.3-hexadiene
  • R ′ is an ethyl group and ⁇ A ′ is 1
  • B 1 is ethenylene
  • n 1 is 0,
  • ⁇ 2 is 0,
  • ⁇ 3 is l
  • R 2 is a compound of the formula III
  • X is a hydrogen atom (No. 3 31)]
  • Trans-4-1 (trans-41-ethylcyclohexyl) cyclohexanic power J-trans (4-E- (trans-1-ethylcyclohexyl) ethenyl) cyclohexanecarbaldehyde instead of aldehyde
  • the title compound was synthesized in the same manner as in Example 1 except that was used as a raw material.
  • Trans-4- (trans-4-ethylcyclohexyl) In the same manner as in Example 1 except that trans-14-formylcyclyl hexyl trans-14-ethylcyclohexanecarboxylate was used as a raw material instead of cyclohexanecarbaldehyde. The title compound was synthesized.
  • Trans-4- (trans-1-ethylcyclohexyl) The title was obtained in the same manner as in Example 1 except that trans-4- (4-ethylphenyl) methoxycyclohexylcarbaldehyde was used as a raw material instead of cyclohexanecarbaldehyde.
  • the compound was synthesized.
  • R 1 is an ethyl group
  • ⁇ 1 is 1,4-cyclohexylene, ⁇ 1 is a covalent bond, ⁇ 1 is 0, ⁇ 2 is 0, ⁇ 3 is 1, R 2 is a compound of formula II and X is a fluorine atom (No. 501) )]
  • X is a fluorine atom (No. 501) )]
  • Example 3 3 1-cyano 1-fluoro-4-1 (trans-1-41 (2- (trans-4-ethylcyclohexyl) ethenyl) cyclohexyl) 1 1 —butene
  • R 1 is an ethyl group and A 1 is 1 , 4-cyclohexylene, B'-hemi-2-ethenylene, 111 is 0, 112 is 0, 113 is 1,
  • R 2 is a compound of the formula II and I is a fluorine atom (No. 5 31)] Manufacturing of
  • R 1 is an ethyl group and A 1 is 1, 4 -safe two alkylene, B 'is 1, 4-butylene, 11 1 0, n 2 is 0, eta 3 is 1, R 2 compounds formula II and X is a fluorine atom (No.
  • R 1 is an ethyl group and A ′ is 1, 4 —Production of a compound (No. 60 1) in which cyclohexylene, B ′ is a covalent bond, n Ui O, n 2 is 0, n 3 is 0, R 2 is formula 11 and X is a fluorine atom
  • Trans-4- (trans-4-ethylcyclohexyl) cyclohexane power (trans-4-1 ⁇ 4-ethylphenyl instead of levalaldehyde) 3- (trans-14-1- (4) synthesized from cyclohexanone —Ethylphenyl) cyclohexyl)
  • the title compound was synthesized in the same manner as in Example 25 except that 121-propenal was used as a raw material.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Liquid Crystal Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Liquid Crystal (AREA)

Abstract

On décrit des dérivé d'acrylonitrile représentés par la formule générale (I), une composition de cristaux liquides contenant un des composés ci-dessus et dont la viscosité et l'anisotropie optique, notamment, sont améliorées, ainsi qu'un afficheur à cristaux liquides préparé avec cette composition. Dans cette formule, A1 à A3 représentent chacun phénylène, cyclohexylène, dioxane ou pyrimidine; R1 représente cyano, halogéno, alkyle, alcoxy, etc.; et R2 représente un groupe correspondant à la formule générale (II) ou (III).
PCT/JP1996/001012 1995-04-14 1996-04-12 Derives d'acrylonitrile, composition de cristaux liquides et afficheur a cristaux liquides WO1996032374A1 (fr)

Priority Applications (3)

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JP53088896A JP3498965B2 (ja) 1995-04-14 1996-04-12 アクリロニトリル誘導体、液晶組成物および液晶表示素子
US08/930,986 US5976408A (en) 1995-04-14 1996-04-12 Acrylonitrile derivative, liquid crystal composition, and liquid crystal display device
EP96909356A EP0820983A4 (fr) 1995-04-14 1996-04-12 Derives d'acrylonitrile, composition de cristaux liquides et afficheur a cristaux liquides

Applications Claiming Priority (2)

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JP7089747A JPH08283226A (ja) 1995-04-14 1995-04-14 アクリロニトリル誘導体、液晶組成物および液晶表示素子
JP7/89747 1995-04-14

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
JP2011084730A (ja) * 2009-09-15 2011-04-28 Chisso Corp 液晶組成物および液晶表示素子
JP2014162751A (ja) * 2013-02-25 2014-09-08 Dic Corp 化合物、液晶組成物、及び表示装置
JP2014162752A (ja) * 2013-02-25 2014-09-08 Dic Corp 化合物、液晶組成物、及び表示装置

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GB9620061D0 (en) * 1996-09-26 1996-11-13 Secr Defence Liquid crystalline (e,e)-butadiene compounds and mixtures and devices containing such compounds
EP0947501A1 (fr) * 1996-11-28 1999-10-06 Chisso Corporation Derives de nitrile conjugues, composes de cristaux liquides, et elements d'affichage a cristaux liquides
KR101779512B1 (ko) 2009-10-06 2017-09-18 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 시클릭 화합물, 이의 제조방법, 감방사선 조성물, 및 레지스트 패턴의 형성 방법
CN105567251B (zh) * 2016-01-13 2018-07-31 石家庄诚志永华显示材料有限公司 液晶组合物

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JPS559012A (en) * 1978-07-05 1980-01-22 Hitachi Ltd Liquid crystal compound
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JPS5770851A (en) * 1980-10-21 1982-05-01 Asahi Glass Co Ltd Cinnamoyl nitrile
JPH02500274A (ja) * 1987-12-30 1990-02-01 パフルユチェンコ，アススヤ　イオシフォフナ 液晶材料の成分としての２，５‐二置換ピリジンの液晶誘導体および液晶材料

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JPS559012A (en) * 1978-07-05 1980-01-22 Hitachi Ltd Liquid crystal compound
JPS5735552A (en) * 1980-08-08 1982-02-26 Asahi Glass Co Ltd Cinnamonitrile compound
JPS5770851A (en) * 1980-10-21 1982-05-01 Asahi Glass Co Ltd Cinnamoyl nitrile
JPH02500274A (ja) * 1987-12-30 1990-02-01 パフルユチェンコ，アススヤ　イオシフォフナ 液晶材料の成分としての２，５‐二置換ピリジンの液晶誘導体および液晶材料

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011084730A (ja) * 2009-09-15 2011-04-28 Chisso Corp 液晶組成物および液晶表示素子
JP2014162751A (ja) * 2013-02-25 2014-09-08 Dic Corp 化合物、液晶組成物、及び表示装置
JP2014162752A (ja) * 2013-02-25 2014-09-08 Dic Corp 化合物、液晶組成物、及び表示装置

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JP3498965B2 (ja) 2004-02-23
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US5976408A (en) 1999-11-02
EP0820983A4 (fr) 1998-11-18

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